Hugh Hefner is living a life that would be a dream of most of the men. A life, that can leave almost anyone jealous.
Hefner's first marriage was with Mildred Williams, from whom he had two children, Christie and David. Mildred had confessed to Hefner about an affair she had prior to their marriage while he was away in the Army. He called the admission "the most devastating moment of my life". A 2006 E! True Hollywood Story profile of Hefner revealed that Mildred allowed him to sleep with other women, out of guilt for her infidelity and in the hopes that it would preserve their marriage. However, they divorced in 1959
After the separation with Mildred, Hefner admitted being "'involved' with some playmates. Donna Michelle, Marilyn Cole, Lillian Müller, Shannon Tweed, Brande Roderick, Barbi Benton, Karen Christy, Sondra Theodore, and Carrie Leigh - who filed a $35 million palimony suit against him - were a few of his many lovers.
Hefner toned down his all-night parties significantly in 1985 after a minor heart attack. In 1989, he married Playmate of the Year Kimberley Conrad. The couple had two sons, Marston Glenn and Cooper Bradford. He and Conrad separated in 1998.
Hefner then began to move an ever-changing coterie of young women into the Mansion, even dating up to seven girls at once, among them, Brande Roderick, Izabella St. James, Tina Marie Jordan, Holly Madison, Bridget Marquardt, and Kendra Wilkinson. For a few years, Kendra Wilkinson, Bridget Marquardt, and Holly Madison were Hugh Hefner's live-in girlfriends, and their relationship was the subject of a hit reality show on E! called "The Girls Next Door". In October 2008, all three girls left the Playboy mansion in Los Angeles where they were living with Hefner. His new "Number One" girlfriend then became Crystal Harris, along with 20-year-old identical twin models Kristina and Karissa Shannon. The relationship with the twins ended in January 2010. Hefner had plans of marrying Crystal on June 18, 2011.
But he was dumped by his fiancée Crystal Harris just five days before their wedding date. She later publicly spoke about their bed room scenes and revealed the reason behind her last minute change of mind on a radio show, claiming that he never turned her on. She also stated that the 85-year-old lasted 'like two seconds' and that he never satisfied her.
The founder of the Playboy Enterprises soon announced the name of the new girlfriend, Shera Bechard who was the Miss November 2010.
Here are a few of the collections of pictures of Hefner and the women in his life.